KR102000301B1 - 산화방지성 염증 조절제로서의 피라졸릴 및 피리미디닐 트리사이클릭 엔온 - Google Patents
산화방지성 염증 조절제로서의 피라졸릴 및 피리미디닐 트리사이클릭 엔온 Download PDFInfo
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- KR102000301B1 KR102000301B1 KR1020137018672A KR20137018672A KR102000301B1 KR 102000301 B1 KR102000301 B1 KR 102000301B1 KR 1020137018672 A KR1020137018672 A KR 1020137018672A KR 20137018672 A KR20137018672 A KR 20137018672A KR 102000301 B1 KR102000301 B1 KR 102000301B1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/47—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of rings being part of condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
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- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| PCT/US2011/065897 WO2012083306A2 (en) | 2010-12-17 | 2011-12-19 | Pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators |
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| PL2252283T3 (pl) | 2008-01-11 | 2019-09-30 | Reata Pharmaceuticals, Inc. | Syntetyczne triterpenoidy i sposoby zastosowania w leczeniu choroby |
| WO2009129546A1 (en) | 2008-04-18 | 2009-10-22 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with amino and other modifications at c-17 |
| CA2721665C (en) | 2008-04-18 | 2017-01-24 | Reata Pharmaceuticals, Inc. | Compounds including an anti-inflammatory pharmacore and methods of use |
| PL2651902T3 (pl) | 2010-12-17 | 2018-04-30 | Reata Pharmaceuticals, Inc. | Pirazolilowe i pirymidynylowe tricykliczne enony jako modulatory zapalenia o działaniu przeciwutleniającym |
| CN103282359A (zh) | 2010-12-17 | 2013-09-04 | 诺华股份有限公司 | 5-氯-n2-(2-异丙氧基-5-甲基-4-哌啶-4-基-苯基)-n4-[2-(丙烷-2-磺酰基)-苯基]-嘧啶-2,4-二胺的结晶形式 |
| JP6410710B2 (ja) | 2012-04-27 | 2018-10-24 | リアタ ファーマシューティカルズ インコーポレイテッド | バルドキソロンメチルの２，２−ジフルオロプロピオンアミド誘導体、その多形体および使用方法 |
| WO2013188818A1 (en) | 2012-06-15 | 2013-12-19 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
| WO2014040060A1 (en) | 2012-09-10 | 2014-03-13 | Reata Pharmaceuticals, Inc. | C17-alkanediyl and alkenediyl derivatives of oleanolic acid and methods of use thereof |
| US9278912B2 (en) | 2012-09-10 | 2016-03-08 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid and methods of use thereof |
| US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| TWI649330B (zh) | 2013-04-24 | 2019-02-01 | 艾伯維有限公司 | 甲基巴多索龍之２，２－二氟丙醯胺衍生物、其多晶形及其使用方法 |
| JP6530758B2 (ja) * | 2014-01-24 | 2019-06-12 | リアタ ファーマシューティカルズ，インク | 抗酸化性炎症調節剤としてのアリールおよびアリールアルキル置換されたピラゾリルおよびピリミジニル三環式エノン類 |
| CN107428698B (zh) * | 2015-02-12 | 2021-10-26 | 里亚塔医药公司 | 作为抗氧化炎症调节剂的咪唑基三环烯酮 |
| KR102486434B1 (ko) | 2016-11-08 | 2023-01-09 | 리아타 파마슈티컬즈 홀딩스, 엘엘씨 | 바독솔론 메틸 또는 이의 유사체를 사용하는 알포트 증후군의 치료 방법 |
| TWI831738B (zh) * | 2016-12-16 | 2024-02-11 | 美商瑞塔醫藥有限責任公司 | 用於抑制ＲＯＲγ及其他用途的嘧啶三環烯酮衍生物 |
| US11286226B2 (en) | 2017-09-21 | 2022-03-29 | Northwestern University | Polycyclic carbogenic molecules and uses thereof as anti-cancer agents |
| WO2019104030A1 (en) * | 2017-11-21 | 2019-05-31 | Biogen Ma Inc. | Tetrahydronaphthalene derivatives useful as nrf2 activators |
| IL279348B2 (en) * | 2018-06-15 | 2026-01-01 | Reata Pharmaceuticals Inc | Decahydro-2h-naphth[1,2-d]imidazole compounds for inhibition of IL-17 and ROR-gamma |
| WO2019246461A1 (en) * | 2018-06-20 | 2019-12-26 | Reata Pharmaceuticals, Inc. | Cysteine-dependent inverse agonists of nuclear receptors ror-gamma/ror-gamma-t and methods of treating diseases or disorders therewith |
| JP2023511302A (ja) | 2020-01-13 | 2023-03-17 | アプタバイオ セラピューティクス インコーポレイテッド | 新規なピラゾール誘導体 |
| US20250025465A1 (en) * | 2021-11-17 | 2025-01-23 | Northwestern University | Wt-idh1 inhibition using a covalent and brain-penetrant small molecular inhibitor for ferroptosis induction in high-grade glioma |
| CN121358860A (zh) * | 2023-06-16 | 2026-01-16 | 南京科捷基因技术有限公司 | 肿瘤特异性表达盒及其用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009146216A2 (en) | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals. Inc. | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
Family Cites Families (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2875201A (en) | 1957-08-28 | 1959-02-24 | Searle & Co | Dehydrotigogenone intermediates |
| US3071577A (en) * | 1959-08-13 | 1963-01-01 | Syntex Corp | Pyrimidinyl androstanes |
| US3994935A (en) | 1975-11-24 | 1976-11-30 | E. R. Squibb & Sons, Inc. | Steroidal 16β-alkyl[16α,17-b]naphthalenes |
| US4395423A (en) | 1978-10-10 | 1983-07-26 | Sterling Drug Inc. | Polycyclic cyanoketones |
| NZ191586A (en) | 1978-10-10 | 1981-10-19 | Sterling Drug Inc | Cyanoketones derived from glycyrrhetinic acid and pharmaceutical compositions |
| CN1013672B (zh) * | 1983-10-03 | 1991-08-28 | 美国辉瑞有限公司 | 2-氨基-5-羟基-4-甲基嘧啶衍生物的制备方法 |
| US5064823A (en) | 1988-08-24 | 1991-11-12 | Research Triangle Institute | Pentacyclic triterpenoid compounds as topoisomerase inhibitors or cell differentiation inducers |
| DE4014171A1 (de) | 1990-05-03 | 1991-11-07 | Basf Ag | Cyanochinolinverbindungen |
| JPH08208479A (ja) * | 1994-04-29 | 1996-08-13 | Takeda Chem Ind Ltd | クラビンアルカロイド誘導体を含有する鎮痛剤 |
| AU2267995A (en) | 1994-04-29 | 1995-11-29 | Takeda Chemical Industries Ltd. | Ergoline derivatives as analgesics |
| KR100418202B1 (ko) * | 1994-09-09 | 2004-07-05 | 쇼죠 고야마 | 분자발현기능의억제방법 |
| US6326507B1 (en) | 1998-06-19 | 2001-12-04 | Trustees Of Dartmouth College | Therapeutic compounds and methods of use |
| US6369101B1 (en) | 1999-02-26 | 2002-04-09 | Regents Of The University Of Minnesota | Therapeutic method to treat herpes virus infection |
| JP5059996B2 (ja) | 1999-05-14 | 2012-10-31 | ネレアス ファーマシューティカルズ インコーポレーテッド | 新規インターロイキン−１および腫瘍壊死因子−αモジュレーター、前記モジュレーターの合成、ならびに前記モジュレーターの使用方法 |
| US6649654B1 (en) | 1999-11-23 | 2003-11-18 | The Regents Of The University Of California | Methods for identifying and using IKK inhibitors |
| US6890946B2 (en) | 1999-12-23 | 2005-05-10 | Indiana University Research And Technology Corporation | Use of parthenolide to inhibit cancer |
| JP4331913B2 (ja) | 2000-02-14 | 2009-09-16 | メルク エンド カムパニー インコーポレーテッド | エストロゲンレセプターモデュレーター |
| JP2001240573A (ja) | 2000-03-01 | 2001-09-04 | Meiji Seika Kaisha Ltd | トリテルペン誘導体及び肝疾患治療剤 |
| WO2002003996A1 (en) | 2000-07-12 | 2002-01-17 | RAJKUMAR, Sujatha | Use of dammarane-type tritepenoid saporins |
| US6951847B2 (en) | 2000-09-29 | 2005-10-04 | Regents Of The University Of Minnesota | Methods of treating fungal infections using lupeol |
| AU2001294953A1 (en) | 2000-09-29 | 2002-04-08 | Regents Of The University Of Minnesota | Triterpenes having fungicidal activity against yeast |
| AU2001294959A1 (en) | 2000-09-29 | 2002-04-08 | Robert M. Carlson | Triterpenes having antibacterial activity |
| US6878751B1 (en) | 2000-10-19 | 2005-04-12 | Imperial College Of Science Technology And Medicine | Administration of resveratrol to treat inflammatory respiratory disorders |
| CA2430454A1 (en) | 2000-11-28 | 2002-06-20 | Board Of Regents, The University Of Texas System | Cddo-compounds and combination therapies thereof |
| US7435755B2 (en) | 2000-11-28 | 2008-10-14 | The Trustees Of Dartmouth College | CDDO-compounds and combination therapies thereof |
| DE60130924T2 (de) * | 2000-12-28 | 2008-07-17 | Ono Pharmaceutical Co. Ltd. | Cyclopentaädüpyrazoloä1,5-aüpyrimidin-verbindung als crf-rezeptor antagonist |
| US20040234977A1 (en) | 2001-05-14 | 2004-11-25 | Da-Wei Gong | Novel alanine transaminase enzyme and methods of use |
| WO2003015761A1 (en) | 2001-08-13 | 2003-02-27 | Merck & Co., Inc. | Selective estrogen receptor modulators |
| MXPA04002667A (es) | 2001-09-19 | 2004-06-18 | Pharmacia Corp | Compuestos de pirazolilo sustituido para el tratamiento de la inflacion. |
| US6991814B2 (en) | 2001-12-13 | 2006-01-31 | Council Of Scientific And Industrial Research | Herbal medicaments for the treatment of neurocerebrovascular disorders |
| DK1465615T3 (da) | 2002-01-15 | 2012-11-12 | Dartmouth College | Tricykliske bisenonderivater og fremgangsmåder til anvendelse heraf |
| JP2005519913A (ja) | 2002-01-18 | 2005-07-07 | リージェンツ オブ ザ ユニバーシティ オブ ミネソタ | 生物学的に活性な表面活性剤としてのトリテルペン第４アンモニウム塩 |
| WO2003081210A2 (en) | 2002-03-21 | 2003-10-02 | Sunesis Pharmaceuticals, Inc. | Identification of kinase inhibitors |
| AU2003303128A1 (en) | 2002-05-13 | 2004-08-13 | Trustees Of Dartmouth College | Inhibitors and methods of use thereof |
| US20050014730A1 (en) | 2003-04-02 | 2005-01-20 | Carlson Robert M. | Anti-fungal formulation of triterpene and essential oil |
| MXPA06002456A (es) | 2003-09-02 | 2006-08-31 | Unigen Pharmaceuticals Inc | Formulacion de una mezcla de flavonoides con el aniillo b libre y flavanos para utilizarse en la prevencion y tratamiento de la declinacion cognoscitiva y el deterioro de la memoria relacionado con la edad. |
| WO2005042002A2 (en) | 2003-10-30 | 2005-05-12 | Entelos, Inc. | Treatment of rhematoid arthritis with flip antagonists |
| WO2005046732A2 (en) | 2003-11-04 | 2005-05-26 | THE UNITED SATES OF AMERICA as represented by THE SECRETARY OF HEALTH AND HUMAN SERVICES, NIH | Methods and compositions for the inhibition of hiv-1 replication |
| US20060258752A1 (en) | 2004-02-12 | 2006-11-16 | Vander Jagt David L | Method and compounds for cancer treatment utilizing NFkB as a direct or ultimate target for small molecule inhibitors |
| JP2005314381A (ja) | 2004-03-30 | 2005-11-10 | Anges Mg Inc | 増殖性腎疾患の予防・治療・改善剤 |
| EP1811840B1 (en) | 2004-09-07 | 2016-04-13 | May Sung Mak | Anti-tumor compounds with angeloyl groups |
| WO2006089406A1 (en) * | 2005-02-22 | 2006-08-31 | Gemin X Biotechnologies Inc. | Diterpenoid compounds, compositions thereof and their use as anti-cancer or anti-fungal agents |
| US7902196B2 (en) | 2005-03-17 | 2011-03-08 | President And Fellows Of Harvard College | Synthesis of avrainvillamide, strephacidin B, and analogues thereof |
| AU2006265113A1 (en) | 2005-07-01 | 2007-01-11 | The Johns Hopkins University | Compositions and methods for the treatment or prevention of disorders relating to oxidative stress |
| DE102005041613A1 (de) | 2005-09-01 | 2007-03-08 | Ergonex Pharma Gmbh | Pharmazeutische Zusammensetzungen zur Behandlung von Karzinoid-Syndrom |
| WO2007112043A2 (en) | 2006-03-23 | 2007-10-04 | Advanced Life Sciences Inc. | Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin |
| WO2007127791A2 (en) | 2006-04-25 | 2007-11-08 | The Administrators Of The Tulane Educational Fund | New pharmacological method for treatment of neuropathic pain |
| EP2032594B1 (en) | 2006-06-27 | 2015-09-23 | Wellington Laboratories Inc. | Glycyrrhetinic acid derivatives |
| JP2008110962A (ja) | 2006-08-02 | 2008-05-15 | Santen Pharmaceut Co Ltd | Ｎｒｆ２活性化物質を有効成分として含む角結膜障害の予防または治療剤 |
| WO2008016095A1 (en) | 2006-08-02 | 2008-02-07 | Santen Pharmaceutical Co., Ltd. | PREVENTIVE OR REMEDY FOR KERATOCONJUNCTIVAL DISORDERS CONTAINING Nrf2 ACTIVATOR AS THE ACTIVE INGREDIENT |
| US8735411B2 (en) | 2006-10-02 | 2014-05-27 | Abbvie Inc. | Macrocyclic benzofused pyrimidine derivatives |
| US20090203661A1 (en) | 2006-10-12 | 2009-08-13 | Safe Stephen H | Betulinic acid, derivatives and analogs thereof and uses therefor |
| US7714012B2 (en) | 2006-11-17 | 2010-05-11 | Trustees Of Dartmouth University | Synthesis and biological activities of new tricyclic-bis-enones (TBEs) |
| US8299046B2 (en) | 2006-11-17 | 2012-10-30 | Trustees Of Dartmouth College | Synthetic triterpenoids and tricyclic-bis-enones for use in stimulating bone and cartilage growth |
| EP2680006A1 (en) | 2007-02-08 | 2014-01-01 | Biogen Idec MA Inc. | Treatment for Amyotrophic Lateral Sclerosis |
| WO2008111497A1 (ja) | 2007-03-08 | 2008-09-18 | Santen Pharmaceutical Co., Ltd. | トリテルペノイドを有効成分として含有する酸化ストレスが関連する眼疾患の予防又は治療剤 |
| WO2008136838A1 (en) | 2007-05-04 | 2008-11-13 | Trustees Of Dartmouth College | Novel amide derivatives of cddo and methods of use thereof |
| US8088824B2 (en) | 2007-08-15 | 2012-01-03 | Reata Pharmaceuticals Inc. | Forms of CDDO methyl ester |
| US20090048205A1 (en) | 2007-08-15 | 2009-02-19 | Colin Meyer | Combination therapy with synthetic triterpenoids and gemcitabine |
| US9012439B2 (en) | 2007-10-29 | 2015-04-21 | University Of Rochester | Use of electrophilic compounds for inducing platelet production or maintaining platelet function |
| PL2252283T3 (pl) | 2008-01-11 | 2019-09-30 | Reata Pharmaceuticals, Inc. | Syntetyczne triterpenoidy i sposoby zastosowania w leczeniu choroby |
| CA2721665C (en) | 2008-04-18 | 2017-01-24 | Reata Pharmaceuticals, Inc. | Compounds including an anti-inflammatory pharmacore and methods of use |
| CN102164941B (zh) | 2008-04-18 | 2015-05-27 | 里亚塔医药公司 | 抗氧化剂炎症调节剂:具有饱和c环的齐墩果酸衍生物 |
| WO2009129546A1 (en) | 2008-04-18 | 2009-10-22 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with amino and other modifications at c-17 |
| RS55631B1 (sr) | 2008-04-18 | 2017-06-30 | Reata Pharmaceuticals Inc | Antioksidansni modulatori upale: c-17 homologisani derivati oleanolinske kiseline |
| US8278311B2 (en) | 2008-04-28 | 2012-10-02 | Abbott Laboratories | Substituted pyrimidine derivatives |
| ES2449396T3 (es) | 2008-07-22 | 2014-03-19 | Trustees Of Dartmouth College | Cianoenonas monocíclicas y métodos de uso de las mismas |
| WO2010053817A1 (en) | 2008-11-04 | 2010-05-14 | Trustees Of Dartmouth College | Betulinic acid derivatives and methods of use thereof |
| SMT201900432T1 (it) | 2009-02-13 | 2019-09-09 | Reata Pharmaceuticals Inc | Composizioni di dosaggio orali, a rilascio ritardato contenenti cddo-me amorfo |
| TWI481607B (zh) | 2009-12-17 | 2015-04-21 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑的２－芳基咪唑衍生物 |
| MX357596B (es) | 2010-04-12 | 2018-07-16 | Reata Pharmaceuticals Inc | Método para tratar obesidad utilizando moduladores de inflamación con antioxidantes. |
| CN102079772A (zh) | 2010-12-09 | 2011-06-01 | 中国药科大学 | 一类五环三萜-13,28-内酯化合物、其制备方法和用途 |
| CN103384470A (zh) | 2010-12-17 | 2013-11-06 | 纳幕尔杜邦公司 | 杀真菌偶氮环酰胺 |
| PL2651902T3 (pl) | 2010-12-17 | 2018-04-30 | Reata Pharmaceuticals, Inc. | Pirazolilowe i pirymidynylowe tricykliczne enony jako modulatory zapalenia o działaniu przeciwutleniającym |
| KR101886467B1 (ko) | 2011-01-31 | 2018-08-07 | 비브 헬스케어 유케이 (넘버4) 리미티드 | Hiv 성숙 억제 활성을 갖는 c-17 및 c-3 변형 트리테르페노이드 |
| SI2683731T1 (sl) | 2011-03-11 | 2019-07-31 | Reata Pharmaceuticals, Inc. | C4-monometil triterpenoidni derivati in postopki njihove uporabe |
| JP6410710B2 (ja) | 2012-04-27 | 2018-10-24 | リアタ ファーマシューティカルズ インコーポレイテッド | バルドキソロンメチルの２，２−ジフルオロプロピオンアミド誘導体、その多形体および使用方法 |
| WO2013188818A1 (en) | 2012-06-15 | 2013-12-19 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
| WO2014040060A1 (en) | 2012-09-10 | 2014-03-13 | Reata Pharmaceuticals, Inc. | C17-alkanediyl and alkenediyl derivatives of oleanolic acid and methods of use thereof |
| US20140088163A1 (en) | 2012-09-10 | 2014-03-27 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| US9278912B2 (en) | 2012-09-10 | 2016-03-08 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid and methods of use thereof |
| BR112016003454B1 (pt) | 2013-08-23 | 2023-02-14 | Reata Pharmaceuticals, Inc. | Uso de composto de metil bardoxolona |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009146216A2 (en) | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals. Inc. | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
Non-Patent Citations (2)
| Title |
|---|
| Bioorganic & Medicinal Chemistry Letters, 1997, 제7권, 제13호, 페이지 1623-1628 |
| Organic Letters, 2010, 제12권, 제3호, 페이지 508-511 |
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